


30 Days of Palletshipping

by thelastdayiwashappy



Category: Pocket Monsters | Pokemon - All Media Types
Genre: 30 Day OTP Porn Challenge, M/M, Other Additional Tags to Be Added
Language: English
Status: In-Progress
Published: 2014-06-24
Updated: 2017-05-30
Packaged: 2018-02-06 02:33:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 3,610
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1841116
Author URL: https://archiveofourown.org/users/thelastdayiwashappy/pseuds/thelastdayiwashappy
Summary: <blockquote class="userstuff">
              <p>The 30 Day NSFW OTP Challenge- Palletshipping edition!</p>
            </blockquote>





	1. Cuddles (Naked)

**Notes for the Chapter:**

> Hello, hello. This is a pretty big “first project” of mine so let’s hope this all goes well. I’ll try and get these out daily, but I can’t guarantee it’ll happen :/ Day 1 is pretty short, my apologies, but the others should be longer! All of these stories take place when the boys are older, just a heads up.

Ash Ketchum was worn out. He had devoted the entire day to training with his Pokemon and the hard work was finally taking its toll. He pulled his sweat-soaked shirt off and kicked his jeans to the floor, flopping onto his bed. As he threw his underwear across the room and pulled the covers over himself, another man entered the room.

He too was covered in sweat from working all day in the yard, sitting on the edge of the bed, running a hand through his auburn spikes. “So what, you’re done for the day?” He laughed, nudging the raven-haired man under the sheets.

“Shut up and get under here,” Ash said, voice muffled by the pillow his face was plastered against.

Gary shrugged out of his lab coat, hanging it in the closet, before throwing the rest of his clothes into the pile with Ash’s and climbing into bed next to the smaller man.

Ash rolled over and wrapped his arms around Gary, burying his face into his chest and mumbling something unintelligible.

“What was that?”

He pulled his head back and looked at the other man, “I said your skin is soft. Sweaty, but soft.” He smiled gently. After working independently on their own projects all day it was nice to come to bed and simply be with each other.

“And you’re sticky and gross,” Gary laughed, ruffling Ash’s hair. “You know, we still have to eat dinner.”

But Ash Ketchum didn’t care. He was perfectly content with dozing off in Gary’s arms for the remainder of the night. He nuzzled his face back against Gary’s chest and quickly fell asleep.


	2. Kisses (Naked)

**Notes for the Chapter:**

> Hello again! I apologize for the wait, writer’s block was kicking my ass. I just realized it’s almost been a month since the first one OTL. Hopefully the next one won’t take as long! Anyway, this one is only a little bit longer than the first, but I promise they’ll keep growing in length. Or they should. I hope you guys don’t mind me throwing in a few of my own headcanons in these, but some I just… can’t resist (Gary needing reading glasses, anyone?). Thank you for waiting patiently and here is day 2~!

Being a researcher wasn’t always a walk in the park. It required a lot of dedication and occasionally staying up until an ungodly hour of the night to finish the work from that day. This was something Gary was willing to put up with.

Ash, however, took this a bit more harshly. The raven-haired boy hated sleeping alone, finding the presence of another comforting. For years Pikachu had sufficed to keep Ash’s need for someone there at night at bay- that was until Gary frequented his bed. Now Ash craved the older boy’s presence.

A night came around where the researcher was forced to continue his work past his usual hours and Ash wasn’t happy about it.

“I won’t be much longer,” Gary had shrugged him off when Ash had attempted to drag him to bed.

That was at 11 PM. Once 2:30 rolled around and Ash had spent three and a half hours fidgeting and falling in and out of sleep. Finally, after waking up for the fourth time, he decided to pester the auburn-haired boy into coming to bed with him again.

He slinked out of bed and hobbled downstairs into the lab that was connected with their house, only to find the researcher still working diligently, reading glasses pushed up the bridge of his nose.

Ash wrapped his arms around Gary’s neck and yawned, “You’re done for the night.”

“I’m almost finished with this paragraph, just give me a few more min-“ he was cut off as Ash grabbed the mouse from his hand and saved the document quickly before shutting down the program.

“No. Bed,” he tugged at Gary’s arm, who sighed, removing his glasses and rubbing his eyes.

“Alright, alright,” he muttered, following the shorter boy into their room and tossing off his clothes before climbing into bed.

Ash snuggled up against him and kissed his collarbone softly, “You need rest.”

Gary tilted Ash’s chin up and kissed him, “I know, I know. Sometimes I just get so caught up in work.”

“You can go back to what you were doing tomorrow,” Ash muttered, gently placing kisses along Gary’s neck.

“I know, I just wanted-” the brunette was cut off as Ash caught Gary’s lips with his own.

“Enough talking,” he kissed him again before snuggling back down.

The brunette sighed, smiling to himself and kissing Ash’s head, “Sweet dreams.”


	3. First Time

**Notes for the Chapter:**

> sup friends i'm not dead just really slow at updating. thank u all so much for waiting i love you  
> 3 drafts later and here you have the latest chapter, which i can at least say is longer than the first two combined?  
> without further ado here is almost 2k of actual porn

To all their friends, Ash and Gary’s first time was a mystery. Not because it was never spoken of, but because the stories recollecting the event that the two told differed vastly and often changed from one telling to another. Both stories seemed equally plausible, so no one could tell whose version was the truth. Neither divulged too much information on the topic, since they preferred to keep their personal lives to themselves; however, they occasionally bickered on the subject, giving away certain details they probably wouldn’t otherwise.

Gary’s retelling of the event generally revolved around the spontaneity of it, since, according to him, they hadn’t been dating, or even discussing the prospect of dating. It was sudden and ridiculously _hot._

 __“It happened one night when we ran into each other in Pallet Town. By then I had already given up training and dedicated my time to research, and it had been quite some time since I had seen Ash. He came to see my grandfather, who wasn’t in at the time, and ran into me in his lab. We talked for a while and I teased him and one thing lead to another. He was a virgin and completely inexperienced, so I had to handle the situation and lend a hand, physically as well as metaphorically,” he added, winking at Ash and smirking, who in turn rolled his eyes at the stupid remark.

 

_Gary interrupted Ash’s protest to the remark he had made against him by slamming their lips together and pulling Ash closer. In shock Ash clumsily stumbled backwards and bumped into the table housing Professor Oak’s current research project._

_“Careful,” Gary chided, moving the project carefully to a nearby counter, “We wouldn’t want to break anything,” he smirked as he turned back to Ash, who was gripping the end of the table, nervous but obviously turned on. Gary walked back to Ash and kissed him again, Ash returning the kiss this time with equal ferocity._

_The table creaked slightly as the two deepened their kiss, Ash wrapping his arms around Gary’s neck and Gary lifting him slightly, enough to lean him against the table more stably. His hands trailed down to the hem of Ash’s shirt, lifting it to run his hands up his smooth skin and tweak a nipple, eliciting a moan from Ash. His face flushed and he tried to cover up his embarrassment with his hands but Gary wasn’t going to let him. He wanted to see Ash’s face; to hear whatever noises he would make._

_Gary lifted Ash’s shirt over his head and leaned in to take his other nipple into his mouth, rolling it with his tongue. He could feel the bulge in Ash’s pants grow and smirked against his nipple, knowing he was making him feel good. Ash tilted his head back and breathed deeply, attempting to stall the orgasm he could already feel coming._

_Sensing this Gary let go of Ash’s nipple with a wet pop, to the other boy’s dismay, and stood up, removing his own shirt before diving back down and kissing Ash again. He trailed kisses down his neck, leaving hickies here and there against his smooth skin. As he did so he reached down and began undoing Ash’s zipper, massaging his bulge through his underwear before pulling them down and pumping his bare length. Ash moaned loudly, whispering Gary’s name._

_Feeling awkward that he was the only one exposed, Ash reached forward and tugged at Gary’s zipper but struggled to pull his pants down from the angle he was at. Gary let go of Ash’s length and helped him remove his own pants, which was a relief from the tightness. He fumbled in the drawers under the counters next to them until he found what he was looking for, procuring a bottle that made Ash even more nervous than before, as well as confused. Now wasn’t the time to ask questions, though, as he noticed Gary squirting some of the lube onto his fingers._

_Ash gulped and Gary leaning in, kissing him softly, “Don’t be nervous, I’ve got you”._

_Ash nodded, though his body tensed as he felt fingers prodding at his entrance. He tried to relax, taking deep breaths as the fingers entered, causing sudden pain to rush through him. The fingers stopped and Gary kissed him again, allowing him to adjust before attempting to push through any further. Once he received a nod that meant the pain had lessened, he slowly pushed further until his fingers were entirely enveloped. He waited again before removing them and pushing in again, seeing the discomfort slowly fade away from Ash’s face and into something that looked more like pleasure. He scissored his fingers and Ash moaned approvingly. Once he felt Ash was ready he added a third finger and opened him up further._

_Gary removed his fingers and grabbed the bottle of lube again, this time coating his own length and positioning himself at Ash’s opening. He steadied himself by holding onto Ash’s hips and slowly pushed in, watching as Ash’s face scrunched up in discomfort he stilled and waited for the discomfort to subside before pushing in even further. Ash was breathing deeply, his head fuzzy from what was happening, when he felt Gary pull out and push in again, grazing a spot that sent shivers down his spine and caused him to moan slightly._

_“Do that again,” he panted, out of breath already._

_Gary grinned and pulled out again, entering with even more force and aiming for the spot that would allow him to hear Ash’s voice loud and clear. He was not disappointed when Ash delivered, nearly yelling._

_The pace Gary set started out slow, allowing himself to fully enjoy being inside of his rival- feeling every inch of him at once. His thrusts became increasingly faster as it was harder for him to keep such a slow pace, in need of release himself. As the pace increased Ash had an even more difficult time keeping his voice down. He grabbed onto the end of the table, curling his fingers around the edge, and attempted to quiet himself by biting into his bottom lip. It became so difficult for him to stifle his moans that he was nearly drawing blood, so he gave in and allowed a small moan escape from his lips._

_Hearing this Gary smirked and thrust harder, causing Ash to moan even louder, despite his best efforts to keep it down. Ash was nearly at his breaking point and Gary could easily tell by the way his breathing had become so labored. He was in a similar position, his orgasm only a few thrusts away. As Gary slammed in once more Ash came, sinking blissfully into the after-glow. He barely felt it when Gary soon followed suit, spilling inside of him and slumping forward, panting._

"That is nowhere _near_ how it went!” Ash shouted, dismissing Gary’s story. Ash told everyone that first time had been a challenge. “He was mocking me, telling me that I wasn’t mature enough to handle such an ‘adult experience’ and so I proved him wrong!”

 

 _They fell to the floor and Gary proceeded to straddle his hips, pinning his hands down above his head by his wrists and licking his bottom lip as he gazed down at him, “Don’t worry, Ashy-boy, I know this is new territory for you, but you’ve got a_ master _here to guide you.”_

_Ash rolled his eyes, staring up at Gary defiantly, “I can handle more than you think,” he spat._

_“Oh, really?” Gary leaned in and kissed him deeply, releasing his arms to allow Ash to wrap them around his neck and deepen the kiss._

 

 __“That was his first mistake!” Ash laughed, faking a pout, “I may look stupid, but I’m far from it!”

 Gary rolled his eyes.

 

_Ash used the temporary moment of weakness on Gary’s part to grab his shoulders and flip them over, allowing himself to straddle Gary and take control. He kissed him again and started undressing him, taking time to run his hands along Gary’s lean yet muscled chest. He left a trail of kisses down his chest and stomach, stopping at his pants to muster up whatever courage he could find within himself. Gary waited patiently, a slight smirk on his face._

_Ash unzipped his pants and swallowed deeply, shocked at how far this had gone. He never expected to be staring down at Gary Oak’s clothed erection, which was obviously already quite large. He ran his hand through his hair nervously before taking a deep breath and pulling his underwear down, revealing Gary’s stiff cock to the open air._

_It was at that point he sat frozen, realizing he honestly had no clue what to do next. As he wracked his brain for what would be the best possible thing to make his rival squirm, as well as proving he wasn’t as innocent as he appeared, Gary sat up and pulled him closer, locking their lips again. He unbuttoned Ash’s jeans and grabbed his cock, pumping it a few times, causing Ash to gasp and moan in shock. He leaned forward, pressing his face into Gary’s shoulder and moaning softly against his skin._

_Gary released Ash’s cock when he was obviously near finishing, pulling him into another kiss and biting Ash’s bottom lip softly, causing him to moan into the kiss. Gary reached over to the pocket of his recently discarded pants and pulled out a packet of lube and a condom._

_“I always come prepared,” he grinned, tearing the packet of lube open and squeezing some onto his finger. He pushed Ash against the bed lightly, nudging his legs apart. “Just remember to relax, okay?” Gary said reassuringly as he eased his slick finger into the other’s hole._

_Ash gritted his teeth at the intrusion but tried to keep his breathing steady, hoping the discomfort would cease. He closed his eyes as he was worked open, a second finger following the first. Before long he was beginning to enjoy the feeling of the fingers, soft moans escaping his throat._

_The fingers pulled out and he groaned, missing the feeling of the digits inside of him._

_Gary shushed him as he steadied himself at Ash’s entrance, pushing in slowly, until he was nearly enveloped in heat. It took all of his effort to not pull out and thrust in again quickly, but he knew Ash needed time to adjust. He pulled out slowly, starting a slow rhythm as he listened to Ash’s moans of approval beneath him._

_The rhythm picked up and despite a small amount of discomfort, Ash was feeling amazing. He lifted his legs and wrapped them around Gary’s back, leaning his head back further and moaning loudly._

_Gary couldn’t help but grin at the sound, thinking of the innocent boy he used to know, knowing he was the one who could cause Ash to make such noises. He picked up the pace, knowing they were both near their end._

_Ash’s breathing became ragged, “I-I think I’m gonna-“_

_“Go ahead,” Gary whispered into his ear, “let it out.”_

_With Gary’s reassurance, Ash came and all he could see was white as the impact of his orgasm hit him. Gary followed quickly after, filling Ash and feeling the bliss wash over him._

_Once the post-orgasm high receded, Gary pulled out and rolled over, breathing heavily. Ash turned and smiled at him, “Next time, I’m gonna make you cum first.”_


	4. Masturbation

**Notes for the Chapter:**

> I didn't mean for Gary jerking off to get so sentimental but shit happens when you write at 5 am

Whenever Gary came back to Pallet for a visit he always hoped that Ash would be there, though he rarely ever was. Professor Oak had even caught on and whenever his grandson came home for a visit, before Gary even asked, he would tell him that, no, Ash wasn’t home, he was wherever he was at the moment, still chasing his dream. Gary missed Pallet but more than anything he missed the stupid boy who’s smiling (or even pouting) face he would get to see.

On one of those visits back to Pallet he spent some time with his grandfather and Tracey, talking trade and discussing where he’d been and what he’d been up to. They showed him the new pokemon that had come to the lab, as well as how his were doing, allowing him to introduce his new pokemon to those he didn’t carry with him anymore. Umbreon always enjoyed these visits as well.

They ate dinner and everything seemed alright, but Gary knew that something was missing and it bothered him.

Umbreon nudged him with her nose and he stood, stretching, before walking to the door and yelling back at his grandpa, “I’m just going for a walk, I’ll be back in a bit!”

His original intention was to go for a walk but before long he found himself standing in front of the Ketchum house, hand raised and prepared to knock.

Before he got the chance the door swung open and Delia Ketchum threw her arms around him, “Gary! Oh my gosh, look at you! It feels like it’s been forever!” She backed up so he could enter.

“How did you—?”

“Oh, I saw you out the kitchen window,” she smiled brightly, walking into the kitchen and back out with a plate of cookies, “I made them this morning.”

He took one and smiled politely, offering his thanks.

“Take a seat,” she said, gesturing to the couch as she sat down across from him. She asked him question after question about how he was doing, what he was doing, was he sleeping and eating alright?

After listening to him talk she excitedly told him what she knew about what Ash was up to before sighing, “That boy seems to be everywhere. I can’t keep track of him these days. He’s not even a boy anymore, but I still worry about him.”

“Do you mind if I go take a look around his room?” Gary blurted out before realizing exactly what he’d said.

“Of course not, go right ahead,” she went back to her housework as he climbed the stairs and entered the small room he remembered vividly from his childhood.

Not much had changed since they were 10 years old, probably to do with the fact that Ash hadn’t been home for long periods of time since then and he seemed to like it the way it was. There were a few things different, including the trophies he earned from various leagues he had placed in and—.

Gary reached out and picked up Ash’s signature hat that he wore when they’d first started their journeys off the desk, sitting down on Ash’s bed and staring at it. Things really hadn’t changed from back then, except how he treated him, since they were friends again. He stroked the brim of the hat absently as his thoughts wandered.

His stomach tightened as certain thoughts returned to him, thoughts that had never really gone away despite the years going by. It didn’t matter what age he was, Gary was still in love with his childhood friend and rival.

Before he fully thought it through he found himself with his hand down his pants, stroking himself, the other clutching the hat tightly. He groaned quietly, closing his eyes and leaning back against the wall.

Ash was in front of him, smiling and looking through his memories with him, hair as messy as ever but there were definitely changes. He’d lost most of the baby-face he’d kept for so long and had a nice frame with muscular arms, but it was that stupid smile that stuck out to Gary the most. He wanted to pull him towards him and press their lips together, to wipe the smile off his face and hear his laughter.

But he wasn’t there, he was somewhere else and this was just Gary’s imagination, which was actually kind of a good thing because in his imagination anything could happen.

He could turn them around and push Ash down onto his bed, straddling him and kissing him deeply, a tint of tongue sneaking in before pulling back and smirking. He could lift Ash’s shirt over his head and move his lips down, starting at his lips, kissing along his jaw, leaving small bites along his neck, and grazing his teeth along his chest. Gary remembered vividly how muscular he had become because it was a constant feature in his dreams. His goofy neighbor and rival had become much less so over the years and that pissed him off and turned him on simultaneously. He wanted to feel those muscles for himself, to kiss him as long as he wanted.

He quickened his pace around his own cock as he imagined Ash pulling off his shirt and unbuttoning his pants, quickly taking him into his mouth. He was pretty sure Ash had never actually sucked a dick before but it didn’t matter, because in this fantasy he was amazing at it. He swallowed him down to the base before looking up at him, brown eyes starting up at him and Gary moaned audibly, coming into his hand and, in his mind, Ash’s mouth. He sat, still leaning against the wall, blissfully embracing the post-orgasm high before he became keenly aware of three things.

He had come up to Ash’s room without him knowing and jacked off on his bed to fantasies of him, which he realized in hindsight was kind of creepy. 

The moan he let out wasn’t very quiet and there was a possibly Delia had heard it.

And last, looking down, he realized he had gotten cum on Ash’s cherished hat.

**Notes for the Chapter:**

> Ending loosely based off [this comic](http://g-r-i-m-a.tumblr.com/post/52780165833)


End file.
